Triethylamine → 4-Chloro-6-(2,4,6-trifluorophenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

HRID 1865913Notes

Reaction equation

HRID 1865913 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[F:13][C:14]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[C:15]=1[NH2:16].CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([NH:16][C:15]2[C:14]([F:13])=[CH:20][C:19]([F:21])=[CH:18][C:17]=2[F:22])[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 677652,4,6-TrifluoroanilineHCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Product 1

HCID 579781024-Chloro-6-(2,4,6-trifluorophenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde [Santilli, et al., J. Heterocycl. Chem. 1971, 8, 445-45] (1.0 gram (hereinafter “g”), 4.48 millimoles (hereinafter “mmol”)) in CHCl3 (20 milliliters (hereinafter “mL”)) was added 2,4,6-tri-fluoroaniline (0.735 g, 5 mmol) followed by Et3N (0.94 mL, 6.72 mmol, 1.5 equivalents (hereinafter “eq”)). The reaction mixture turned yellow and was heated at 50° C. for 8 hours (hereinafter “h”), 1 M aq Na2CO3 solution (50 mL) was added and the layers were separated. The organic layer was washed with 50 ml sat'd. aqueous (hereinafter “satd aq”) NaCl solution, dried through anhydrous MgSO4 and evaporated. The crude product was purified by flash chromatography (Hex/AcOEt=95/5) to afford 1.3 g (87%) of pure 4-chloro-6-(2,4,6-trifluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde.

Workup

  1. additionwas added
  2. customthe layers were separated
  3. washThe organic layer was washed with 50 ml
  4. dry with materialdried through anhydrous MgSO4
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (Hex/AcOEt=95/5)

Sources & evidence

ORD record
ord-21a91584572343e4b7ce219b4c388bba
Source dataset
uspto-grants-2009_12
Patent number
US07629350B2

Reaction notes

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